Herbicidal cyclic sulfonamides of phenoxybenzoic acids

ABSTRACT

There are provided herbicidal cyclic sulfonamides of phenoxybenzoic acids.

BACKGROUND OF THE INVENTION

Herbicidal 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoic acid and salts thereof, and various herbicidal derivatives of these compounds have been proposed including alkyl and cycloalkyl esters, alkylthio esters, phenyl ester, alkyl and dialkyl amido and benzoyl chloride forms. U.S. Pat. which describe such compounds and the like include U.S. Pat. Nos. 3,652,645; 3,784,635; 3,873,302; 3,983,168; 3,907,866; 3,798,276; 3,928,416; and 4,063,929.

SUMMARY OF THE INVENTION

This invention provides certain herbicidal compounds of the formula: ##STR1## where: (i) Y₁ is N or CH;

(ii) Y₂ is N or CX₄ ; provided that Y₁ is not N when Y₂ is CX₄ ; and

(iii) X₁, X₂, X₃, X₄ and R are groups which are capable of being incorporated into formula I and which collectively impart herbicidal activity thereto.

With respect to compounds of formula I which are capable of forming salts (e.g., where R is H), the invention also provides agronomically acceptable salts (e.g., alkali metal salts such as sodium salts or ammonium salts, e.g, of the formula (C₁ -C₆ alkyl)_(n) NH_(4-n) (where n is 0-4) of compounds of formula I.

Examples of the groups X₁, X₂, X₃, X₄ and R are as follows:

X₁ and X₂ may be the same or different and may be selected from the group consisting of halo (e.g., Cl, Br or F) or CF₃ ;

X₃ may be NO₂ or halo (e.g., Cl, Br or F);

X₄ may be H, halo (e.g., Cl, Br or F) or CF₃ ; and

R may be H or substituted or unsubstituted hydrocarbyl (e.g., having from 1 to 12 carbon atoms such as C₁ -C₁₂ alkyl).

A preferred form of forumula I is represented by the formula ##STR2##

Preferred compounds according to the present invention are: ##STR3## and sodium, potassium and ammonium salts of formula III.

Compounds of formula I may be prepared by

(1) Oxidation of the appropriate benzyl mercaptan to the sulfonic acid: ##STR4## (2) Formation of the cyclic amide: ##STR5##

The compounds of this invention can be applied in various ways to achieve herbicidal action. They can be applied per se, but may be applied as the toxic components in pesticidal compositions of the compound and a carrier. These compositions may be applied directly to the soil and often incorporated therewith. The compositions can be applied as granulars or dusts; as liquid sprays, or as gas-propelled sprays and can contain, in addition to a carrier, additives such as emulsifying agents, binding agents, gases compressed to the liquid state, odorants, stabilizers, and the like. A wide variety of liquid and solid carriers can be used. Non-limiting examples of solid carriers include talc, bentonite, diatomaceous earth, pyrophyllite, fullers earth, gypsum, flours derived from cottom seeds and nut shells, and various natural and synthetic clays having a pH not exceeding about 9.5. Non-limiting examples of liquid carriers include water, organic solvents such as alcohols, ketones, light oils, and medium oils and vegetable oils such as cottonseed oil. In practice, herbicidal application is measured in terms of pounds of herbicide applied per acre. The compounds of this invention are effective herbicides when applied in herbicidal amounts, e.g., at rates between about 0.03 pound and about 10 pounds per acre. 

What is claimed is:
 1. A herbicidal compound of the formula: ##STR6## where: (i) Y₁ is N or CH;(ii) Y₂ is N or CX₄, provided that Y₁ is not N when Y₂ is CX₄ ; (iii) X₁ and X₂ are the same or different and selected from the group consisting of halogen or CF₃ ; (iv) X₃ is NO₂ or halogen; (v) X₄ is H, halogen or CF₃ ; and (vi) R is H or C₁ to C₁₂ alkyl.
 2. A herbicidal compound of the formula: ##STR7## wherein: R is H or a C₁ to C₁₂ alkyl.
 3. A herbicidal compound selected from the group consisting of: ##STR8## and sodium, potassium and ammonium salts of formula III.
 4. A herbicidal composition comprising an effective amount of a compound according to any one of claims 1 to 3, and an agronomically acceptable carrier.
 5. A method for combating unwanted plants which comprises contacting them with a herbicidally effective amount of a compound according to any one of claims 1 to
 3. 